A novel route to substituted 3-methylidenechroman-2-ones and 3-methylchromen-2-ones |
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| Authors: | Tomasz Janecki Tomasz W?sek |
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| Affiliation: | Department of Chemistry, Institute of Organic Chemistry, Technical University of ?ód?, ?eromskiego 116, 90-924 ?ód?, Poland |
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| Abstract: | 3-Methylidenechroman-2-ones, or their rearrangement products 3-methylchromen-2-ones, were efficiently synthesized by Michael addition of various nucleophiles to 3-diethoxyphosphorylchromen-2-ones followed by Horner-Wadsworth-Emmons reaction of the adducts with formaldehyde. Relative configuration and conformation of the intermediate adducts were studied using NMR spectroscopy and semiempirical PM3 calculations. |
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| Keywords: | Chroman-2-ones Michael addition Horner-Wadsworth-Emmons olefination |
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